3,3'-(m-Phenyl-enedi-oxy)diphthalonitrile.

In the title compound, C(22)H(10)N(4)O(2), the dihedral angles between the mean planes of the central benzene ring and the pendant rings are 79.20 (6) and 80.29 (6)°. The dihedral angle between the pendant rings is 10.27 (7)°.

Related literature

For background to ‘semi-rigid’ mol­ecules as ligands, see: Wang et al. (2005 ▶, 2009 ▶). For related structures, see: Huang et al. (2005 ▶); Zhang & Lu (2007 ▶).

Experimental

Crystal data

C22H10N4O2

M = 362.34

Monoclinic,

a = 15.668 (3) Å

b = 12.722 (3) Å

c = 19.004 (5) Å

β = 109.911 (6)°

V = 3561.7 (14) Å3

Z = 8

Mo Kα radiation

μ = 0.09 mm−1

T = 298 K

0.20 × 0.15 × 0.10 mm

Data collection

Bruker SMART 1000 CCD diffractometer

Absorption correction: multi-scan (SADABS; Siemens, 1996 ▶) T min = 0.982, T max = 0.991

10307 measured reflections

3992 independent reflections

3145 reflections with I > 2σ(I)

R int = 0.034

Refinement

R[F 2 > 2σ(F 2)] = 0.039

wR(F 2) = 0.111

S = 1.03

3992 reflections

254 parameters

H-atom parameters constrained

Δρmax = 0.20 e Å−3

Δρmin = −0.16 e Å−3

Data collection: SMART (Siemens, 1996 ▶); cell refinement: SAINT (Siemens, 1996 ▶); data reduction: SAIn class="Chemical">NT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: SHELXTL (Sheldrick, 2008 ▶); software used to prepare material for publication: SHELXTL.

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536810011578/hb5363sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536810011578/hb5363Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C22H10N4O2	F(000) = 1488
Mr = 362.34	Dx = 1.351 Mg m−3
Monoclinic, C2/c	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: -C 2yc	Cell parameters from 4716 reflections
a = 15.668 (3) Å	θ = 2.6–27.4°
b = 12.722 (3) Å	µ = 0.09 mm−1
c = 19.004 (5) Å	T = 298 K
β = 109.911 (6)°	Rod, yellow
V = 3561.7 (14) Å3	0.20 × 0.15 × 0.10 mm
Z = 8

Bruker SMART 1000 CCD diffractometer	3992 independent reflections
Radiation source: fine-focus sealed tube	3145 reflections with I > 2σ(I)
graphite	Rint = 0.034
ω scans	θmax = 27.6°, θmin = 2.1°
Absorption correction: multi-scan (SADABS; Siemens, 1996)	h = −14→20
Tmin = 0.982, Tmax = 0.991	k = −15→15
10307 measured reflections	l = −24→23

Refinement on F2	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.039	H-atom parameters constrained
wR(F2) = 0.111	w = 1/[σ2(Fo2) + (0.0506P)2 + 1.0114P] where P = (Fo2 + 2Fc2)/3
S = 1.03	(Δ/σ)max < 0.001
3992 reflections	Δρmax = 0.20 e Å−3
254 parameters	Δρmin = −0.16 e Å−3
0 restraints	Extinction correction: SHELXL97 (Sheldrick, 2008), Fc*=kFc[1+0.001xFc2λ3/sin(2θ)]-1/4
Primary atom site location: structure-invariant direct methods	Extinction coefficient: 0.0032 (4)

Geometry. All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
C2	0.24878 (8)	0.23670 (11)	0.58469 (7)	0.0496 (3)
O1	0.41988 (6)	0.16069 (8)	0.64684 (5)	0.0597 (3)
O2	0.73624 (5)	0.20407 (7)	0.70914 (6)	0.0582 (3)
C9	0.49526 (7)	0.15184 (9)	0.62398 (7)	0.0425 (3)
C10	0.57791 (7)	0.17608 (9)	0.67719 (7)	0.0437 (3)
H10	0.5826	0.1926	0.7260	0.052*
C20	0.88271 (8)	0.16165 (10)	0.78616 (7)	0.0438 (3)
C11	0.65301 (7)	0.17492 (9)	0.65542 (7)	0.0459 (3)
C14	0.48704 (8)	0.12738 (10)	0.55183 (7)	0.0474 (3)
H14	0.4308	0.1110	0.5168	0.057*
C3	0.26451 (7)	0.12567 (10)	0.58820 (6)	0.0420 (3)
C4	0.19286 (7)	0.05388 (10)	0.56020 (6)	0.0443 (3)
C15	0.79734 (7)	0.12689 (9)	0.74065 (7)	0.0448 (3)
C12	0.64815 (9)	0.15132 (11)	0.58405 (8)	0.0554 (3)
H12	0.7000	0.1512	0.5707	0.067*
N3	0.23572 (10)	0.32515 (11)	0.58276 (8)	0.0727 (4)
C21	0.90124 (8)	0.27171 (11)	0.79679 (8)	0.0535 (3)
C8	0.35196 (8)	0.08751 (11)	0.61986 (7)	0.0466 (3)
C16	0.77924 (9)	0.02090 (10)	0.73059 (8)	0.0558 (3)
H16	0.7222	−0.0022	0.7005	0.067*
C5	0.20892 (9)	−0.05263 (11)	0.56674 (8)	0.0528 (3)
H5	0.1612	−0.1000	0.5485	0.063*
C19	0.95031 (8)	0.08725 (11)	0.82021 (7)	0.0499 (3)
C13	0.56427 (9)	0.12762 (11)	0.53235 (8)	0.0543 (3)
H13	0.5597	0.1115	0.4835	0.065*
N2	1.11044 (8)	0.15377 (13)	0.89675 (8)	0.0774 (4)
C1	0.10262 (8)	0.09249 (11)	0.52163 (8)	0.0524 (3)
C6	0.29672 (9)	−0.08846 (11)	0.60074 (8)	0.0585 (3)
H6	0.3077	−0.1604	0.6061	0.070*
C18	0.93170 (10)	−0.01859 (12)	0.80996 (8)	0.0630 (4)
H18	0.9762	−0.0681	0.8328	0.076*
C17	0.84594 (11)	−0.05017 (12)	0.76525 (9)	0.0661 (4)
H17	0.8332	−0.1216	0.7585	0.079*
C22	1.03960 (9)	0.12385 (12)	0.86413 (8)	0.0577 (4)
N4	0.03136 (8)	0.12171 (11)	0.48961 (8)	0.0725 (4)
C7	0.36803 (9)	−0.01905 (12)	0.62679 (8)	0.0564 (3)
H7	0.4269	−0.0441	0.6490	0.068*
N1	0.91780 (9)	0.35902 (11)	0.80612 (9)	0.0809 (4)

	U11	U22	U33	U12	U13	U23
C2	0.0399 (6)	0.0575 (8)	0.0501 (7)	−0.0042 (6)	0.0137 (5)	−0.0057 (6)
O1	0.0322 (4)	0.0797 (7)	0.0681 (6)	−0.0119 (4)	0.0181 (4)	−0.0269 (5)
O2	0.0293 (4)	0.0448 (5)	0.0869 (7)	−0.0052 (3)	0.0020 (4)	−0.0088 (4)
C9	0.0287 (5)	0.0456 (6)	0.0512 (7)	−0.0002 (4)	0.0111 (5)	−0.0022 (5)
C10	0.0347 (6)	0.0455 (6)	0.0463 (6)	−0.0043 (5)	0.0080 (5)	−0.0018 (5)
C20	0.0333 (6)	0.0515 (7)	0.0468 (6)	−0.0069 (5)	0.0137 (5)	−0.0004 (5)
C11	0.0286 (5)	0.0389 (6)	0.0635 (8)	−0.0048 (4)	0.0071 (5)	−0.0023 (5)
C14	0.0357 (6)	0.0514 (7)	0.0482 (7)	−0.0012 (5)	0.0056 (5)	−0.0031 (5)
C3	0.0334 (5)	0.0526 (7)	0.0406 (6)	−0.0027 (5)	0.0134 (5)	−0.0007 (5)
C4	0.0323 (6)	0.0554 (7)	0.0442 (6)	−0.0035 (5)	0.0117 (5)	0.0026 (5)
C15	0.0326 (5)	0.0463 (7)	0.0540 (7)	−0.0043 (5)	0.0129 (5)	−0.0004 (5)
C12	0.0422 (7)	0.0545 (7)	0.0764 (9)	−0.0084 (6)	0.0290 (6)	−0.0085 (7)
N3	0.0745 (9)	0.0599 (8)	0.0802 (9)	0.0003 (7)	0.0219 (7)	−0.0093 (6)
C21	0.0306 (6)	0.0589 (8)	0.0642 (8)	−0.0086 (5)	0.0076 (5)	−0.0030 (6)
C8	0.0313 (5)	0.0621 (8)	0.0462 (6)	−0.0049 (5)	0.0128 (5)	−0.0072 (5)
C16	0.0443 (7)	0.0484 (7)	0.0661 (8)	−0.0098 (6)	0.0077 (6)	0.0010 (6)
C5	0.0432 (7)	0.0544 (8)	0.0602 (8)	−0.0089 (6)	0.0168 (6)	0.0020 (6)
C19	0.0383 (6)	0.0640 (8)	0.0453 (6)	−0.0011 (6)	0.0116 (5)	0.0054 (6)
C13	0.0537 (7)	0.0589 (8)	0.0534 (7)	−0.0065 (6)	0.0223 (6)	−0.0070 (6)
N2	0.0416 (7)	0.1071 (11)	0.0731 (8)	−0.0068 (7)	0.0059 (6)	0.0123 (8)
C1	0.0369 (6)	0.0569 (8)	0.0581 (7)	−0.0078 (6)	0.0094 (6)	0.0031 (6)
C6	0.0523 (8)	0.0527 (8)	0.0718 (9)	0.0046 (6)	0.0229 (7)	0.0087 (7)
C18	0.0578 (8)	0.0600 (9)	0.0630 (8)	0.0099 (7)	0.0098 (7)	0.0136 (7)
C17	0.0674 (9)	0.0459 (7)	0.0737 (9)	−0.0043 (6)	0.0093 (8)	0.0075 (7)
C22	0.0395 (7)	0.0768 (10)	0.0532 (7)	0.0029 (6)	0.0111 (6)	0.0111 (7)
N4	0.0399 (6)	0.0705 (8)	0.0914 (10)	−0.0021 (6)	0.0018 (6)	0.0083 (7)
C7	0.0360 (6)	0.0694 (9)	0.0617 (8)	0.0092 (6)	0.0140 (6)	0.0056 (7)
N1	0.0538 (7)	0.0594 (8)	0.1145 (12)	−0.0151 (6)	0.0094 (8)	−0.0088 (8)

C2—N3	1.1421 (19)	C15—C16	1.3777 (18)
C2—C3	1.4315 (19)	C12—C13	1.3798 (19)
O1—C8	1.3750 (15)	C12—H12	0.9300
O1—C9	1.3949 (14)	C21—N1	1.1406 (19)
O2—C15	1.3596 (15)	C8—C7	1.377 (2)
O2—C11	1.4048 (14)	C16—C17	1.369 (2)
C9—C14	1.3686 (17)	C16—H16	0.9300
C9—C10	1.3795 (16)	C5—C6	1.3828 (19)
C10—C11	1.3740 (16)	C5—H5	0.9300
C10—H10	0.9300	C19—C18	1.377 (2)
C20—C15	1.3946 (16)	C19—C22	1.4406 (18)
C20—C19	1.4035 (18)	C13—H13	0.9300
C20—C21	1.4303 (19)	N2—C22	1.1369 (18)
C11—C12	1.3657 (19)	C1—N4	1.1368 (16)
C14—C13	1.3808 (18)	C6—C7	1.377 (2)
C14—H14	0.9300	C6—H6	0.9300
C3—C8	1.3834 (16)	C18—C17	1.382 (2)
C3—C4	1.4038 (16)	C18—H18	0.9300
C4—C5	1.3761 (19)	C17—H17	0.9300
C4—C1	1.4393 (17)	C7—H7	0.9300
N3—C2—C3	178.96 (15)	N1—C21—C20	178.61 (16)
C8—O1—C9	117.33 (9)	O1—C8—C7	122.54 (11)
C15—O2—C11	118.00 (9)	O1—C8—C3	116.79 (12)
C14—C9—C10	121.99 (11)	C7—C8—C3	120.59 (11)
C14—C9—O1	121.98 (10)	C17—C16—C15	119.49 (12)
C10—C9—O1	115.89 (11)	C17—C16—H16	120.3
C11—C10—C9	117.60 (11)	C15—C16—H16	120.3
C11—C10—H10	121.2	C4—C5—C6	119.28 (12)
C9—C10—H10	121.2	C4—C5—H5	120.4
C15—C20—C19	119.07 (12)	C6—C5—H5	120.4
C15—C20—C21	120.25 (11)	C18—C19—C20	120.26 (12)
C19—C20—C21	120.67 (11)	C18—C19—C22	121.00 (13)
C12—C11—C10	122.52 (11)	C20—C19—C22	118.73 (13)
C12—C11—O2	120.25 (11)	C12—C13—C14	121.25 (12)
C10—C11—O2	117.16 (11)	C12—C13—H13	119.4
C9—C14—C13	118.43 (11)	C14—C13—H13	119.4
C9—C14—H14	120.8	N4—C1—C4	178.29 (16)
C13—C14—H14	120.8	C7—C6—C5	120.85 (13)
C8—C3—C4	118.83 (12)	C7—C6—H6	119.6
C8—C3—C2	119.73 (11)	C5—C6—H6	119.6
C4—C3—C2	121.43 (10)	C19—C18—C17	119.06 (13)
C5—C4—C3	120.56 (11)	C19—C18—H18	120.5
C5—C4—C1	119.98 (11)	C17—C18—H18	120.5
C3—C4—C1	119.41 (12)	C16—C17—C18	121.77 (14)
O2—C15—C16	124.39 (11)	C16—C17—H17	119.1
O2—C15—C20	115.27 (10)	C18—C17—H17	119.1
C16—C15—C20	120.34 (11)	N2—C22—C19	177.82 (15)
C11—C12—C13	118.21 (12)	C8—C7—C6	119.83 (12)
C11—C12—H12	120.9	C8—C7—H7	120.1
C13—C12—H12	120.9	C6—C7—H7	120.1
C8—O1—C9—C14	41.14 (17)	C9—O1—C8—C3	−129.48 (12)
C8—O1—C9—C10	−143.02 (12)	C4—C3—C8—O1	−179.70 (10)
C14—C9—C10—C11	−0.04 (18)	C2—C3—C8—O1	0.21 (16)
O1—C9—C10—C11	−175.87 (11)	C4—C3—C8—C7	−2.83 (18)
C9—C10—C11—C12	0.24 (18)	C2—C3—C8—C7	177.08 (12)
C9—C10—C11—O2	177.36 (10)	O2—C15—C16—C17	−179.83 (13)
C15—O2—C11—C12	−77.49 (16)	C20—C15—C16—C17	−0.4 (2)
C15—O2—C11—C10	105.33 (13)	C3—C4—C5—C6	−0.51 (19)
C10—C9—C14—C13	−0.24 (19)	C1—C4—C5—C6	176.87 (12)
O1—C9—C14—C13	175.35 (12)	C15—C20—C19—C18	−1.39 (19)
C8—C3—C4—C5	2.48 (17)	C21—C20—C19—C18	179.66 (13)
C2—C3—C4—C5	−177.43 (11)	C15—C20—C19—C22	176.97 (12)
C8—C3—C4—C1	−174.92 (11)	C21—C20—C19—C22	−1.98 (18)
C2—C3—C4—C1	5.17 (17)	C11—C12—C13—C14	−0.1 (2)
C11—O2—C15—C16	−8.46 (19)	C9—C14—C13—C12	0.3 (2)
C11—O2—C15—C20	172.12 (11)	C4—C5—C6—C7	−1.1 (2)
C19—C20—C15—O2	−179.22 (11)	C20—C19—C18—C17	0.6 (2)
C21—C20—C15—O2	−0.27 (17)	C22—C19—C18—C17	−177.77 (14)
C19—C20—C15—C16	1.32 (19)	C15—C16—C17—C18	−0.4 (2)
C21—C20—C15—C16	−179.72 (13)	C19—C18—C17—C16	0.4 (2)
C10—C11—C12—C13	−0.2 (2)	O1—C8—C7—C6	177.91 (12)
O2—C11—C12—C13	−177.18 (11)	C3—C8—C7—C6	1.2 (2)
C9—O1—C8—C7	53.72 (17)	C5—C6—C7—C8	0.8 (2)